Vacation rentals in Stamford

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Top-rated vacation rentals in Stamford

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Top guest favorite
A chalet-style home is surrounded by lush greenery, featuring a large three-sided wrap-around deck. Tall windows dominate the front, allowing ample natural light. To the side, a wooden garage complements the main structure, set against a backdrop of trees and an expansive lawn.
Chalet in Stamford
4.94 out of 5 average rating, 132 reviews

Peaceful VT Chalet w/ Mountain View’s

Our Peaceful chalet has everything you need. A fully equipped kitchen, 3 bedrooms, 2.5 baths, 2 living rooms, elec heat fireplace, outdoor fire pit, washer, dryer, Roku TV’s, great fiber optic internet. Accessible ATV/ snowmobile trails from property. 20 miles to Mt. Snow. Short driving distance to popular golf courses, shops, restaurants,breweries, kayaking, fishing, hiking, white water rafting ect An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

Top guest favorite
A spacious living area features modern seating arrangements with natural light streaming through large glass windows. A small table is set by the window, overlooking the garden. Polished wooden floors and decorative items add warmth to the inviting atmosphere.
Guesthouse in Marlboro Township
4.97 out of 5 average rating, 187 reviews

Refined, serene and like no other, Marlboro, VT.

Our elegant, supremely comfortable, and private guesthouse is surrounded by a wonderful garden and 350 acres of woodland in the quiet of rural Vermont. We are 30 minutes from Brattleboro to the east, with its many shops and restaurants, and 12 minutes from the small town of Wilmington to our west, with some restaurants, shops, and a supermarket However, we always recommend bringing groceries, etc., for your first night and next morning. We are pleased to offer a 20% discount for 7 days or more!

Top guest favorite
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford
4.95 out of 5 average rating, 152 reviews

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 398 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favorite
Cabin in Shaftsbury
4.99 out of 5 average rating, 328 reviews

The Hygge Loft- mid-mod cabin on 70 acres w/HotTub

The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

Top guest favorite
A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.
Home in Bennington
5 out of 5 average rating, 134 reviews

The Vermont Farmhouse|Hiking|Dog Trails|Village

Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

Guest favorite
A cozy bedroom is filled with natural light from two windows, dressed with blue curtains. A spacious bed with striped bedding is centered in the room. A white dresser and a television are positioned along the walls, creating a relaxing atmosphere.
Apartment in Stamford
4.88 out of 5 average rating, 354 reviews

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Escape to our cozy apartment in picturesque Southern Vermont! Featuring a comfortable bedroom, a well-equipped kitchenette, a private bathroom, and a charming dining area, this space has everything you need for a relaxing stay. Enjoy the perfect blend of tranquility and easy access—just a scenic 10-minute drive brings you to North Adams, MA, home to Mass MoCA, MCLA, and plenty of dining and shopping. Book now for the ideal balance of serenity and convenience!

Top guest favorite
An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.
Cottage in Shaftsbury
4.98 out of 5 average rating, 777 reviews

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Superhost
A uniquely designed raised container home features multiple levels and large windows that offer expansive views of the surrounding landscape. The structure includes a covered outdoor area below, and the combination of dark wood and metal creates a striking exterior appearance.
Shipping container in Whitingham
4.87 out of 5 average rating, 119 reviews

The House of Pi

WE now pay your 15.5% Guest Service fee!!! Welcome to The House of Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!

Top guest favorite
A living area features a stone fireplace with a roaring fire, surrounded by large windows that invite natural light. A circular coffee table rests on a textured rug, while comfortable seating options include an upholstered chair and wooden accent chairs, complemented by soft lighting.
Cottage in Bennington
4.98 out of 5 average rating, 122 reviews

Cozy, bright 3-bedroom Cottage with fireplace.

Cozy, spacious brook-side cottage with 3 bedrooms, 2 baths, fully-equipped kitchen, fireplace, and serene, 382-acre country setting. Colorful artwork, designer furnishings, and well-appointed kitchen and bathrooms will make you feel welcome and at home. Historic charm of Bennington ten minutes away. NYC (182 miles); Boston (118); Mt. Snow (32); Prospect Mountain (13). Close to MASS MoCA (22), Tanglewood (49) and Manchester outlets (32).

Top guest favorite
Two wooden chairs are positioned on a grassy area, facing a gently sloping hill. A modern white farmhouse is visible alongside a deck with stairs. In the background, trees frame the serene landscape, and mountains are faintly visible under a cloudy sky.
Apartment in Bennington
4.92 out of 5 average rating, 200 reviews

Scenic Vermont Studio

This beautiful retreat is halfway between the ski slopes of southern Vermont and the cultural centers of Williamstown and North Adams, MA. The residence is a modern, spacious, basement apartment, part of an 1860 farm house. It has its own private entrance around the back of the house at ground level. Solar garden lights and motion detector lighting will illuminate your path to the apartment.

Top guest favorite
A white farmhouse-style structure is set on a lush green hill, surrounded by a clear blue sky. The building features a gabled roof, multiple windows, and a small cupola. A neat lawn frames the house, emphasizing its inviting exterior.
Home in Bennington
4.99 out of 5 average rating, 352 reviews

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

Popular amenities for Stamford vacation rentals